781-05-5Relevant academic research and scientific papers
Regioselective Epoxidations by Cytochrome P450 3A4 Using a Theobromine Chemical Auxiliary to Predictably Produce N-Protected β- or γ-Amino Epoxides
Polic, Vanja,Cheong, Kin Jack,Hammerer, Fabien,Auclair, Karine
supporting information, p. 3983 - 3989 (2017/11/30)
N-Protected β- and γ-amino epoxides are useful chiral synthons. We report here that the enzyme cytochrome P450 3A4 can catalyze the formation of such compounds in a regio- and stereoselective manner, even in the presence of multiple double bonds or aromatic substituents. To this end, the theobromine chemical auxiliary is used not only to control the selectivity of the enzyme, but also as a masked amine, and to facilitate product recovery. Theobromine predictably directed epoxidation at the double bond of the fourth carbon from the theobromine group. Unlike with most catalysts, the selectivity did not depend on electronic or steric factors but rather on the position of the olefin relative to the theobromine group. (Figure presented.).
A Functional-Group-Tolerant Catalytic trans Hydrogenation of Alkynes
Radkowski, Karin,Sundararaju, Basker,Fuerstner, Alois
supporting information, p. 355 - 360 (2013/02/23)
Against the rules: During the hundred years following Sabatier's groundbreaking work on catalytic hydrogenation, syn delivery of the H atoms to the π system of a substrate remained the governing stereochemical rule. An exception has now be found with the
A detailed investigation of the aza-prins reaction
Dobbs, Adrian P.,Guesne, Sebastien J. J.,Parker, Robert J.,Skidmore, John,Stephenson, Richard A.,Hursthouse, Mike B.
supporting information; experimental part, p. 1064 - 1080 (2010/06/13)
The development of a Lewis acid-promoted aza-Prins reaction to form piperidines and pyrrolidines is described. Indium trichloride has been found to be a highly successful and mild Lewis acid for promoting this reaction. A thorough mechanistic investigation is described, including the factors that influence the formation of the 5- or 6-membered ring product(s). The Royal Society of Chemistry.
